Chappelle’s Show’s Coolest Cameos

Everyone knows that Chappelle’s Show had a way with absurd characters and social commentary, but there’s one area in which the show hasn’t gotten its proper due: casting. Budding superstar comedians? Got ’em. Legendary rappers? Check. Iconic movie stars? Oh, hell yeah.

These days, he’s the ultimate comic’s comic, but Burr was just a budding stand-up trying to make a name for himself when he was cast as a dude ordering a beer beside Chappelle’s Samuel L. Jackson. Little did we know back then that Burr’s own talent for yelling would give Jackson a run for his money.

Brennan co-created Chappelle’s Show — and even appeared in a few episodes, playing such iconic roles as the guy welcoming Dave to the club in slow motion. Those dance moves should have clued us in to the fact that Brennan was a star just waiting to be discovered.

When Dave was considering quitting the show, he called up the Outkast rapper for some advice, proving once again that even his most casual acquaintances are more impressive than literally anyone we’ve ever met. (Also in this sketch: cool dad Nick Cannon.)

Sarandon is many things: a timeless movie star, an outspoken activist, and – in the role she’ll most likely be remembered for — the lover of Chappelle’s Lil’ Jon. That’s right: Just when you thought she couldn’t get more awesome, Sarandon cozied up in bed with one of Chappelle’s most outrageous characters for some sex and sandwich talk. This woman has a sense of humor — and an Oscar.